JPH075671B2 - Method for producing polyacetylene - Google Patents
Method for producing polyacetyleneInfo
- Publication number
- JPH075671B2 JPH075671B2 JP19821088A JP19821088A JPH075671B2 JP H075671 B2 JPH075671 B2 JP H075671B2 JP 19821088 A JP19821088 A JP 19821088A JP 19821088 A JP19821088 A JP 19821088A JP H075671 B2 JPH075671 B2 JP H075671B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- linear hydrocarbon
- acetylene
- substrate
- polyacetylene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims description 20
- 229920001197 polyacetylene Polymers 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 150000002430 hydrocarbons Chemical class 0.000 claims description 21
- 239000004215 Carbon black (E152) Substances 0.000 claims description 20
- 229930195733 hydrocarbon Natural products 0.000 claims description 20
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 18
- 239000000758 substrate Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 8
- 238000001179 sorption measurement Methods 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical group Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims 1
- 239000010408 film Substances 0.000 description 18
- 150000000475 acetylene derivatives Chemical class 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical group CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- LLCSWKVOHICRDD-UHFFFAOYSA-N buta-1,3-diyne Chemical group C#CC#C LLCSWKVOHICRDD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000002305 electric material Substances 0.000 description 1
- 230000005660 hydrophilic surface Effects 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical class Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Composite Materials (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Polymerisation Methods In General (AREA)
Description
【発明の詳細な説明】 産業上の利用分野 本発明は、電気材料に関するもので、さらに詳しくは、
電気伝導性や非線形光学効果を示すポリアセチレン結合
を有する有機材料の製造方法に関するものである。TECHNICAL FIELD The present invention relates to an electric material, and more specifically,
The present invention relates to a method for producing an organic material having a polyacetylene bond that exhibits electrical conductivity and a nonlinear optical effect.
従来の技術 アセチレン誘導体のポリマーは、π電子共役系を持つた
め、電気伝導性や非線形光学効果を示すことから、電気
機能材料、光学機能材料として広く研究されている。2. Description of the Related Art Polymers of acetylene derivatives have a π-electron conjugated system and thus exhibit electrical conductivity and nonlinear optical effects, and are widely studied as electrical functional materials and optical functional materials.
これまでのポリアセチレンの製造方法としては、白川法
と呼ばれる触媒を利用した重合法がよく知られている。As a conventional method for producing polyacetylene, a polymerization method using a catalyst called Shirakawa method is well known.
一方、クロルシラン基を直鎖状炭化水素鎖の末端にもつ
アセチレン誘導体を用いれば、液相化学吸着法によりオ
ングストロームオーダーの超薄膜であるアセチレン誘導
体の単分子膜を形成でき、さらに、累積膜を形成するこ
ともできる。On the other hand, if an acetylene derivative having a chlorosilane group at the end of a linear hydrocarbon chain is used, it is possible to form a monomolecular film of the acetylene derivative, which is an ultra-thin angstrom-order thin film, by the liquid-phase chemisorption method, and further form a cumulative film. You can also do it.
発明が解決しようとする課題 ところが、第２図に示すごとく、単に化学吸着法により
アセチレン誘導体の単分子膜を基板100上に形成しただ
けでは、単分子膜101を形成している直鎖状炭化水素分
子内のアセチレン基102の向きが、各々の分子で様々な
方向を向いており、そののちのエネルギービームの照射
による重合反応では、重合によって形成される共役二重
結合の形成方向が、アセチレン基の向きによるため、一
方向に長い共役二重結合を持つポリアセチレンを形成で
きる可能性はほとんどなく、また、それを解決する方法
も見いだされていなかった。However, as shown in FIG. 2, when a monomolecular film of an acetylene derivative is simply formed on the substrate 100 by the chemisorption method, the linear carbonized film forming the monomolecular film 101 is formed. The orientation of the acetylene group 102 in the hydrogen molecule is oriented in various directions in each molecule, and in the subsequent polymerization reaction by irradiation with the energy beam, the formation direction of the conjugated double bond formed by the polymerization is acetylene. Due to the orientation of the groups, there is little possibility of forming polyacetylene having a conjugated double bond that is long in one direction, and no method for solving it has been found.
課題を解決するための手段 本発明では、直鎖状炭化水素分子の末端にクロルシラン
基を有し、かつ、任意の位置にアセチレン基および、分
極率の大きい置換基、または、不対電子をもつ置換基を
有する有機分子を溶解させた溶液中に、親水性の任意の
基板を浸漬させ、前記基板上に化学吸着法によりアセチ
レン誘導体の単分子膜を形成する。つぎに、前記基板上
に形成された単分子膜に対して、所定の角度で、また、
所定の強度の磁場をかける。つぎに、前記基板上の前記
単分子膜にエネルギービームを照射して重合反応を行
う。この時も、単分子膜に対して、所定の角度で、ま
た、所定の強度の磁場をかける。以上の処理によりポリ
アセチレンを形成する。Means for Solving the Problems In the present invention, a linear hydrocarbon molecule has a chlorosilane group at the terminal and has an acetylene group and a substituent having a large polarizability or an unpaired electron at an arbitrary position. An arbitrary hydrophilic substrate is immersed in a solution in which an organic molecule having a substituent is dissolved, and a monomolecular film of an acetylene derivative is formed on the substrate by a chemisorption method. Next, with respect to the monomolecular film formed on the substrate, at a predetermined angle,
Apply a magnetic field of a predetermined intensity. Next, the monomolecular film on the substrate is irradiated with an energy beam to carry out a polymerization reaction. Also at this time, a magnetic field having a predetermined angle and a predetermined strength is applied to the monomolecular film. Polyacetylene is formed by the above treatment.
作用 本発明で用いるアセチレン基を持つ直鎖状炭化水素分子
には分極率の大きい基、または、不対電子持つ基があ
り、外部からかけられる磁場の角度およびその強度に応
じて前記の基の向きが定められる。したがって、基板上
に形成された前記有機分子に磁場をかけると前記基の向
きが一定となり、そのため、前記直鎖状炭化水素分子の
炭素原子および水素分子の立体的位置は一意的に定ま
る。同時に、前記直鎖状炭化水素分子内のアセチレン基
の立体的向きも一意的に定まる。この状態はすべての直
鎖状炭化水素分子に共通であるため、すべてのアセチレ
ン基の立体的向きは同一方向となり、非常に整った単分
子膜が形成される。この状態で、エネルギービームを前
述した単分子膜に照射して、アセチレンモノマーを重合
反応させポリアセチレンを形成する。磁場をかけること
により、非常に長い共役二重結合を持つポリアセチレン
を形成することができる。Action The linear hydrocarbon molecule having an acetylene group used in the present invention includes a group having a large polarizability or a group having an unpaired electron. The orientation is fixed. Therefore, when a magnetic field is applied to the organic molecule formed on the substrate, the orientation of the group becomes constant, so that the steric positions of the carbon atom and hydrogen molecule of the linear hydrocarbon molecule are uniquely determined. At the same time, the steric orientation of the acetylene group in the linear hydrocarbon molecule is uniquely determined. Since this state is common to all linear hydrocarbon molecules, the steric directions of all acetylene groups are in the same direction, and a very ordered monomolecular film is formed. In this state, the monomolecular film described above is irradiated with the energy beam to polymerize the acetylene monomer to form polyacetylene. By applying a magnetic field, polyacetylene having a very long conjugated double bond can be formed.
実施例 以下に、本発明の実施例を模式図面を用いて詳細に説明
する。Example Hereinafter, an example of the present invention will be described in detail with reference to the schematic drawings.
本実施例では不対電子をもつ直鎖状炭化水素分子を用い
た例を示す。In this embodiment, an example using a linear hydrocarbon molecule having an unpaired electron will be shown.
本発明に使用したアセチレン基を含む直鎖状炭化水素分
子はω−トリコシノイックトリクロロシラン誘導体（CH
≡Ｃ−CHCN−（CH2）19−SiCl2）で、３位の位置の炭素
原子にはCN基が配位し、また、分子鎖末端にはクロルシ
ラン基が配位している。前記直鎖状炭化水素分子をｎ−
ヘキサデカンを主体とする溶液に溶解させ、容器10内に
化学吸着液１を作成する。つぎに、表面が親水性の任意
の基板、たとえば、表面が酸化されたAl基板または酸化
シリコン膜の形成されたSi基板２を化学吸着液１に浸漬
し、直鎖状炭化水素分子を化学吸着法にて吸着させて基
板２上に単分子吸着膜３を形成する。このとき、−SiCl
基と基板表面のSiO2とともに形成されている−OH基とが
脱塩酸反応して、基板表面に の単分子膜が形成される。（第１図ａ） つぎに、エネルギービームとして、たとえば、前記基板
全面に電子線４を照射して前記直鎖状炭化水素分子内の
アセチレン基５を重合させる。このとき、電子線照射と
同時に前記基板に対して所定の角度で、磁場６を印加す
る。磁場の影響により、前記炭化水素分子内のCN基の不
対電子により磁場に対して一定の方向を向く。したがっ
て、前記直鎖状炭化水素分子内にあるアセチレン基５の
立体的向きも一意的に定められる。このアセチレン基の
立体的向きはすべての直鎖状炭化水素分子内のアセチレ
ン基に共通である。よって、この状態でエネルギービー
ムを照射することにより共役二重結合の非常に長いポリ
アセチレン７が形成される。（第１図ｂ、ｃ） なお、本発明の実施例では、アセチレン基を含む直鎖状
炭化水素分子としてω−トリコシノイック酸（CH≡Ｃ−
（CH2）20−COOH）誘導体を用いたが、これに関わら
ず、アセチレン基を含むその他の直鎖状炭化水素分子で
あってもよい。The linear hydrocarbon molecule containing an acetylene group used in the present invention is a ω-tricosinoic trichlorosilane derivative (CH
In ≡C-CHCN- (CH 2) 19 -SiCl 2), CN group is coordinated to the carbon atom of the 3-position, also the end of the molecular chain chlorosilanes group is coordinated. The linear hydrocarbon molecule is n-
Hexadecane is dissolved in a solution containing mainly hexadecane to prepare a chemical adsorption liquid 1 in the container 10. Next, an arbitrary substrate having a hydrophilic surface, for example, an Al substrate having an oxidized surface or a Si substrate 2 having a silicon oxide film formed thereon is immersed in the chemical adsorbent 1 to chemically adsorb linear hydrocarbon molecules. Method to adsorb the monomolecular adsorption film 3 on the substrate 2. At this time, -SiCl
-OH group formed together with the SiO 2 on the substrate surface undergoes a dehydrochlorination reaction to leave a residue on the substrate surface. Is formed. (FIG. 1a) Next, as an energy beam, for example, the entire surface of the substrate is irradiated with an electron beam 4 to polymerize the acetylene group 5 in the linear hydrocarbon molecule. At this time, the magnetic field 6 is applied to the substrate at a predetermined angle simultaneously with the electron beam irradiation. Under the influence of the magnetic field, unpaired electrons of the CN group in the hydrocarbon molecule are oriented in a certain direction with respect to the magnetic field. Therefore, the steric orientation of the acetylene group 5 in the linear hydrocarbon molecule is also uniquely determined. The steric orientation of this acetylene group is common to all acetylene groups in a linear hydrocarbon molecule. Therefore, irradiation with an energy beam in this state forms polyacetylene 7 having a very long conjugated double bond. (FIG. 1 b, c) In the examples of the present invention, ω-tricosinoic acid (CH≡C-) was used as a linear hydrocarbon molecule containing an acetylene group.
(CH 2) was used 20-COOH) derivatives, regardless thereto, but may be other linear hydrocarbon molecules containing an acetylene group.
また、不対電子をもつ基として本発明の実施例では、CN
基の例を示したが、分極率の大きい基であっても良く、
その例として−Cl、−Ｆ、-NO2基、−CHO基などであっ
てもよい。Further, in the embodiment of the present invention, as a group having an unpaired electron, CN
Although an example of a group is shown, a group having a large polarizability may be used,
For example, it may be -Cl, -F, -NO 2 group, -CHO group or the like.
さらに、不対電子を持つ基として本発明の実施例では−
CN基の例を示したが、その他の不対電子を持ち、高スピ
ン多重度を有する置換基であればよい。Further, in the embodiment of the present invention, as a group having an unpaired electron,
Although the example of the CN group is shown, any other substituent having an unpaired electron and having high spin multiplicity may be used.
さらになお、本発明の実施例では、アセチレンの電子線
照射により機能性膜としてポリアセチレンを形成する例
を示したが、そのほか、様々な機能性膜を形成できる。
その例として、ジアセチレンの重合反応によりポリアセ
チレンを形成することができる。Furthermore, in the embodiment of the present invention, an example in which polyacetylene is formed as a functional film by electron beam irradiation of acetylene has been shown, but other various functional films can be formed.
As an example, polyacetylene can be formed by the polymerization reaction of diacetylene.
さらにまた、本発明の実施例では、磁場を用いて直鎖状
炭化水素分子の配列を整列したが、そのほか、電場を用
いて直鎖状炭化水素分子の配列を整列してもよい。Furthermore, in the embodiment of the present invention, the alignment of the linear hydrocarbon molecules is aligned using the magnetic field, but in addition, the alignment of the linear hydrocarbon molecules may be aligned using the electric field.
さらにさらになお、本発明の実施例では、単分子膜によ
る例を示したが、累積膜であっても本発明による効果が
得られることは明白である。Furthermore, in the embodiment of the present invention, the example using a monomolecular film is shown, but it is clear that the effect of the present invention can be obtained even with a cumulative film.
発明の効果 本発明を用いることにより、電気伝導性や非線形光学効
果の優れたポリアセチレンを効率よく製造することがで
きる。さらに、この製造方法では、理論的には共役二重
結合が連続して形成できるため、従来得られなかった非
常に長い直鎖状の超高分子量のポリアセチレンの製造も
可能であるため、非線形光学効果を利用したデバイスの
製作には極めて有効である。また、超共役二重結合は超
伝導性を有すると考えられており、本発明により常温超
伝導物質が製作できる可能性がある。EFFECTS OF THE INVENTION By using the present invention, polyacetylene excellent in electric conductivity and nonlinear optical effect can be efficiently produced. Furthermore, in this manufacturing method, since conjugated double bonds can theoretically be continuously formed, it is possible to manufacture a very long linear ultra-high molecular weight polyacetylene that has not been obtained in the past, and thus nonlinear optical It is extremely effective for manufacturing a device utilizing the effect. Further, the superconjugated double bond is considered to have superconductivity, and there is a possibility that a room-temperature superconducting substance can be manufactured by the present invention.
第１図ａ、ｂ、ｃは本発明の実施例のポリアセチレン製
造工程を示す模式図、第２図は従来例を示す模式図であ
る。 １……化学吸着液、２……Si基板、３……単分子吸着
膜、４……電子線、５……アセチレン基、６……磁場、
７……ポリアセチレン。1 (a), 1 (b) and 1 (c) are schematic views showing the polyacetylene production process of the embodiment of the present invention, and FIG. 2 is a schematic view showing a conventional example. 1 ... Chemical adsorption liquid, 2 ... Si substrate, 3 ... Monomolecular adsorption film, 4 ... Electron beam, 5 ... Acetylene group, 6 ... Magnetic field,
7 ... Polyacetylene.
Claims (3)
基を有し、主鎖の任意の位置にアセチレン基（−Ｃ≡Ｃ
−）を有する有機分子を溶解させた溶液中に親水性を有
する任意の基板を浸漬させ、化学吸着法により前記基板
上に前記有機分子の単分子膜を形成させる工程と、前記
基板上に形成された前記単分子膜に磁場を印加する工程
と、エネルギービームを前記単分子膜に照射し前記有機
分子内のアセチレン基を重合させる工程とからなること
を特徴としたポリアセチレンの製造方法。1. A linear hydrocarbon molecule having a chlorosilane group at one end and an acetylene group (-C≡C) at any position of the main chain.
Forming a monomolecular film of the organic molecule on the substrate by a chemical adsorption method by immersing an arbitrary substrate having hydrophilicity in a solution in which the organic molecule having −) is dissolved; And a step of irradiating the monomolecular film with an energy beam to polymerize the acetylene group in the organic molecule, the method for producing polyacetylene.
率の大きい置換基を持つことを特徴とした特許請求の範
囲第１項に記載のポリアセチレンの製造方法。2. The method for producing polyacetylene according to claim 1, wherein the linear hydrocarbon molecule has a substituent having a large polarizability at an arbitrary position.
電子を持つ置換基を持つことを特徴とした特許請求の範
囲第１項に記載のポリアセチレンの製造方法。3. The method for producing polyacetylene according to claim 1, wherein the linear hydrocarbon molecule has a substituent having an unpaired electron at an arbitrary position.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19821088A JPH075671B2 (en) | 1988-08-09 | 1988-08-09 | Method for producing polyacetylene |
| US07/347,213 US5019303A (en) | 1988-05-11 | 1989-05-04 | Process for producing polyacetylene |
| DE8989108432T DE68905518T2 (en) | 1988-05-11 | 1989-05-10 | METHOD FOR PRODUCING POLYACETYLENE. |
| EP89108432A EP0341697B1 (en) | 1988-05-11 | 1989-05-10 | Process for producing polyacetylene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19821088A JPH075671B2 (en) | 1988-08-09 | 1988-08-09 | Method for producing polyacetylene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0247108A JPH0247108A (en) | 1990-02-16 |
| JPH075671B2 true JPH075671B2 (en) | 1995-01-25 |
Family
ID=16387320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19821088A Expired - Lifetime JPH075671B2 (en) | 1988-05-11 | 1988-08-09 | Method for producing polyacetylene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH075671B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7204486B2 (en) | 2003-03-31 | 2007-04-17 | Fujifilm Corporation | Sheet discharging apparatus |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2649856B2 (en) * | 1990-04-13 | 1997-09-03 | 松下電器産業株式会社 | Nonlinear optical material |
| JP5340040B2 (en) * | 2009-06-04 | 2013-11-13 | キヤノン株式会社 | Membrane containing conjugated polymer chain and method for producing the same |
| JP6331828B2 (en) * | 2014-07-24 | 2018-05-30 | セントラル硝子株式会社 | Composite silica film, coating liquid for forming composite silica film, and method for forming composite silica film using the same |
-
1988
- 1988-08-09 JP JP19821088A patent/JPH075671B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7204486B2 (en) | 2003-03-31 | 2007-04-17 | Fujifilm Corporation | Sheet discharging apparatus |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0247108A (en) | 1990-02-16 |
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